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ES2238679T3 - AMIDAS OF SUBSTITUTED AROMATIC THIOCARBOXYLIC ACIDS AND THEIR USE AS HERBICIDES. - Google Patents

AMIDAS OF SUBSTITUTED AROMATIC THIOCARBOXYLIC ACIDS AND THEIR USE AS HERBICIDES.

Info

Publication number
ES2238679T3
ES2238679T3 ES95917347T ES95917347T ES2238679T3 ES 2238679 T3 ES2238679 T3 ES 2238679T3 ES 95917347 T ES95917347 T ES 95917347T ES 95917347 T ES95917347 T ES 95917347T ES 2238679 T3 ES2238679 T3 ES 2238679T3
Authority
ES
Spain
Prior art keywords
carbon atoms
alkyl
substituted
fluorine
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
ES95917347T
Other languages
Spanish (es)
Inventor
Karl-Heinz Linker
Kurt Findeisen
Roland Andree
Mark-Wilhelm Drewes
Andreas Lender
Otto Schallner
Wilhelm Haas
Hans-Joachim Santel
Markus Dollinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19500439A external-priority patent/DE19500439A1/en
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Application granted granted Critical
Publication of ES2238679T3 publication Critical patent/ES2238679T3/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
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    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/40—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

LA INVENCION TRATA DE NUEVAS AMIDAS AROMATICAS SUSTITUIDAS DE ACIDOS TIOCARBOXILIOCOS DE FORMULA GENERAL (I), EN DONDE R{SUP,1}, R{SUP,2} Y R{SUP,3} SON HIDROGENO O DIFERENTES SUSTITUYENTES, Y Z ES UN HETEROCICLILO, HETEROCICLIL-AMINO O HETEROCICLIL-IMINO, OPCIONALMENTE SUSTITUIDOS, MONO- O BICICLICOS, SATURADOS O INSATURADOS; Y SU UTILIZACION COMO HERBICIDAS.THE INVENTION IS ABOUT NEW AROMATIC AMIDAS REPLACED THIOCARBOXYLIOC ACIDS OF GENERAL FORMULA (I), WHERE R {SUP, 1}, R {SUP, 2} YR {SUP, 3} ARE HYDROGEN OR DIFFERENT SUBSTITUTES, YZ IS A HETERO HETEROCICLIL-AMINO OR HETEROCICLIL-IMINO, OPTIONALLY SUBSTITUTED, MONO- OR BICYCLE, SATURATED OR INSURED; AND ITS USE AS HERBICIDES.

Description

Amidas de ácidos tiocarboxílicos aromáticas substituidas y su empleo como herbicidas.Amides of aromatic thiocarboxylic acids substituted and its use as herbicides.

La invención se refiere a nuevas amidas de ácidos tiocarboxílicos aromáticas substituidas, a procedimientos para su obtención y a su empleo como herbicidas.The invention relates to new acid amides substituted aromatic thiocarboxylics, to procedures for their obtaining and its use as herbicides.

Se sabe ya que determinadas carbotioamidas aromáticas, tal como por ejemplo la 2,6-dicloro-benzotioamida ("clorotiamida") presentan propiedades herbicidas (véase la publicación GB-PS 987 253). En la publicación EP-A 0 370 332 se describen N-aril-heterociclos nitrogenados con actividad herbicida, que se diferencian de los compuestos según la invención porque tienen un resto ciano en lugar de un resto de amida de ácido tiocarboxílico. Sin embargo, la actividad de este compuesto, conocido con anterioridad, no es completamente satisfactoria en todos los campos de aplicación especialmente en el caso de cantidades de aplicación y concentraciones bajas.It is already known that certain carbothioamides aromatic, such as the 2,6-dichloro-benzothioamide ("chlorothiamide") have herbicidal properties (see GB-PS publication 987 253). In the publication EP-A 0 370 332 are described Nitrogenous N-aryl heterocycles with herbicidal activity, which differ from the compounds according to the invention because they have a cyano moiety instead of an amide moiety of thiocarboxylic acid. However, the activity of this compound, previously known, is not completely satisfactory in all fields of application especially in the case of application quantities and low concentrations.

Se han encontrado ahora las nuevas amidas aromáticas de ácidos tiocarboxílicos, substituidas, de la fórmula general (I),The new amides have now been found aromatics of thiocarboxylic acids, substituted, of the formula general (I),

1one

en la quein the that

R^{1}R1
significa hidrógeno, flúor, cloro o bromo,means hydrogen, fluorine, chlorine or bromine,

R^{2}R2
significa el agrupamiento siguiente,means the following grouping,

\quadquad
-A^{1}-A^{3}-A 1 -A 3

A^{1}A1
significa oxígeno, azufre o el agrupamiento -N-A^{4}-, donde A^{4} significa hidrógeno, alquilo con 1 a 4 átomos de carbono, alcoxi con 1 a 4 átomos de carbono o alquilsulfonilo con 1 a 4 átomos de carbono,means oxygen, sulfur or clustering -N-A 4 -, where A 4 means hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 atoms of carbon or alkylsulfonyl with 1 to 4 carbon atoms,

A^{3}A3
significa hidrógeno, hidroxi, amino, ciano, isocianato, tiocianato, nitro, carboxi, carbamoilo, tiocarbamoilo, sulfo, clorosulfonilo, halógeno, significa alquilo, alcoxi, alquiltio, alquilsulfinilo, alquilsulfonilo, alquilamino, dialquilamino, alcoxicarbonilo o dialcoxi(tio)fosforilo con, respectivamente, 1 a 6 átomos de carbono en los grupos alquilo, substituidos respectivamente en caso dado por halógeno o alcoxi con 1 a 4 átomos de carbono, significa alquenilo, alqueniloxi, alquenilamino, alquilidenamino, alqueniloxicarbonilo, alquinilo, alquiniloxi, alquinilamino o alquiniloxicarbonilo con, respectivamente, 2 a 6 átomos de carbono en los grupos alquenilo, alquilideno o alquinilo, substituidos respectivamente, en caso dado, por halógeno, significa, cicloalquilo, cicloalquiloxi, cicloalquilalquilo, cicloalquilalcoxi, cicloalquilidenamino, cicloalquiloxicarbonilo o cicloalquilalcoxicarbonilo con, respectivamente, 3 a 6 átomos de carbono en los grupos cicloalquilo y, en caso dado, 1 a 4 átomos de carbono en los grupos alquilo, substituidos respectivamente, en caso dado, por halógeno, por ciano, por carboxi, por alquilo con 1 a 4 átomos de carbono y/o por alcoxicarbonilo con 1 a 4 átomos de carbono, o significa fenilo, feniloxi, fenil-alquilo con 1 a 4 átomos de carbono, fenil-alcoxi con 1 a 4 átomos de carbono, feniloxicarbonilo o fenil-alcoxicarbonilo con 1 a 4 átomos de carbono, substituidos respectivamente, en caso dado, por nitro, por ciano, por carboxi, por halógeno, por alquilo con 1 a 4 átomos de carbono, halógenoalquilo con 1 a 4 átomos de carbono, por alquiloxi con 1 a 4 átomos de carbono, halógenoalquiloxi con 1 a 4 átomos de carbono y/o alcoxi-carbonilo con 1 a 4 átomos de carbono, pirrolilo, pirazolilo, imidazolilo, triazolilo, furilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, oxadiazolilo, tiadiazolilo, piridinilo, pirimidinilo, triazinilo, pirazolil-alquilo con 1 a 4 átomos de carbono, furil-alquilo con 1 a 4 átomos de carbono, tienil-alquilo con 1 a 4 átomos de carbono, oxazolil-alquilo con 1 a 4 átomos de carbono, isoxazol-alquilo con 1 a 4 átomos de carbono, tiazol-alquilo con 1 a 4 átomos de carbono, piridinil-alquilo con 1 a 4 átomos de carbono, isoxazol-alquilo con 1 a 4 átomos de carbono, tiazol-alquilo con 1 a 4 átomos de carbono, piridinil-alquilo con 1 a 4 átomos de carbono, isoxazol-alquilo con 1 a 4 átomos de carbono, tiazol-alquilo con 1 a 4 átomos de carbono, piridinil-alquilo con 1 a 4 átomos de carbono, pirimidinil-alquilo con 1 a 4 átomos de carbono, pirazolilmetoxi, furilmetoxi (respectivamente hidrogenados en caso dado total o parcialmente), significa perhidropiranilmetoxi o piridilmetoxi,means hydrogen, hydroxy, amino, cyano, isocyanate, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl with, respectively, 1 to 6 carbon atoms in the alkyl groups, substituted respectively if necessary by halogen or alkoxy with 1 to 4 atoms carbon, means alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkylamino or alkynyloxycarbonyl with, respectively, 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, respectively, if necessary, substituted by halogen, it means, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl with, respectively, 3 to 6 atoms of carbon in the cycloalkyl groups and, where appropriate, 1 to 4 atoms of carbon in the alkyl groups, substituted respectively, in case given, by halogen, by cyano, by carboxy, by alkyl with 1 to 4 carbon atoms and / or alkoxycarbonyl with 1 to 4 atoms of carbon, or means phenyl, phenyloxy, phenyl-alkyl with 1 to 4 carbon atoms, phenyl-alkoxy with 1 to 4 carbon atoms, phenyloxycarbonyl or phenyl-alkoxycarbonyl with 1 to 4 carbon atoms, respectively substituted, if necessary, by nitro, by cyano, by carboxy, by halogen, by alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, by alkyloxy with 1 to 4 carbon atoms, halogenoalkyloxy with 1 to 4 carbon atoms and / or alkoxycarbonyl with 1 to 4 carbon atoms, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-alkyl with 1 to 4 carbon atoms, furyl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazolyl-alkyl with 1 to 4 carbon atoms, isoxazol-alkyl with 1 to 4 carbon atoms, thiazol-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, isoxazol-alkyl with 1 to 4 carbon atoms, thiazol-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, isoxazol-alkyl with 1 to 4 carbon atoms, thiazol-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, pyrimidinyl-alkyl with 1 to 4 carbon atoms, pyrazolylmethoxy, furylmethoxy (respectively hydrogenated in case given totally or partially), means perhydropyranylmethoxy or pyridylmethoxy,

R^{3}R 3
significa hidrógeno, flúor, cloro, bromo, ymeans hydrogen, fluorine, chlorine, bromine, Y

ZZ
significa el agrupamiento heterocíclico indicado a continuación,means the heterocyclic grouping indicated to continuation,

22 

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip

en el queat that

Q^{1}Q1
significa -CO- o -CS-,means -CO- or -CS-,

R^{6}R 6
significa diflúormetilo o triflúormetilo, ymeans diflumoromethyl or trifluoromethyl, Y

R^{7}R 7
significa metilo, etilo, n-o i-propilo o diflúormetilo.means methyl, ethyl, n-o i-propyl or difluoromethyl.

Se obtienen las nuevas amidas aromáticas de ácidos tiocarboxílicos, substituidas, de la fórmula general (I), si se hace reaccionar nitrilos aromáticos de la fórmula general (II)The new aromatic amides of thiocarboxylic acids, substituted, of the general formula (I), if aromatic nitriles of the general formula are reacted (II) 

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip

33 

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip

en la quein the that

R^{1}, R^{2}, R^{3} y Z 

\;
tienen los significados anteriormente indicados,R 1, R 2, R 3 and Z 
 \;
they have the meanings indicated above,

con ácido sulfhídrico (sulfuro de hidrógeno, H_{2}S) o con tioacetamida en caso dado en presencia de un agente auxiliar de la reacción y en caso dado en presencia de un diluyente.with hydrogen sulfide ( hydrogen, H 2 S) or with thioacetamide if necessary in the presence of an auxiliary reaction agent and if necessary in the presence of a diluent

Las nuevas amidas aromáticas de ácidos tiocarboxílicos, substituidas, de la fórmula general (I) se caracterizan por una actividad herbicida potente y selectiva.The new aromatic acid amides thiocarboxylic, substituted, of the general formula (I) is characterized by a potent and selective herbicidal activity.

Las cadenas hidrocarbonadas saturadas o insaturadas en las definiciones, tales como alquilo, alcanodiilo, alquenilo o alquinilo -también en combinación con heteroátomos tales como en alcoxi, alquiltio o alquilamino- son, respectivamente, de cadena lineal o de cadena ramificada.The saturated hydrocarbon chains or unsaturated in the definitions, such as alkyl, alkanediyl, alkenyl or alkynyl - also in combination with such heteroatoms as in alkoxy, alkylthio or alkylamino- are, respectively, of linear or branched chain.

En general, halógeno significa flúor, cloro, bromo o yodo, preferentemente significa flúor, cloro o bromo, especialmente significa flúor o cloro.In general, halogen means fluorine, chlorine, bromine or iodine, preferably means fluorine, chlorine or bromine, especially means fluorine or chlorine.

El objeto de la invención son, preferentemente, los compuestos de la fórmula (I), en la queThe object of the invention are preferably the compounds of the formula (I), in which

R^{1}R1
significa hidrógeno, flúor o cloro,means hydrogen, fluorine or chlorine,

R^{2}R2
significa el agrupamiento siguiente,means the following grouping,

\quadquad
-A^{1}- A^{3}-A 1 - A 3

\quadquad
en el quein which

A^{1}A1
significa oxígeno, azufre o el agrupamiento -N-A^{4}-, donde A^{4} significa hidrógeno, metilo, etilo, n- o i-propilo, metoxi, etoxi, n- o i-propoxi, metilsulfonilo o etilsulfonilo,means oxygen, sulfur or clustering -N-A 4 -, where A 4 means hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,

A^{3}A3
significa hidrógeno, hidroxi, amino, ciano, nitro, carboxi, carbamoilo, sulfo, flúor, cloro, bromo, significa, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, n-, i-, s- o t-pentilo, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, n-, i-, s- o t-pentiloxi, metiltio, etiltio, n- o i-propiltio, n-, i- s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, n- o i-propilsulfonilo, metilamino, etilamino, n- o i-propilamino, n-, i-, s- o t-butilamino, dimetilamino, dietilamino, metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, dimetoxifosforilo, dietoxifosforilo, dipropoxifosforilo o diisopropoxifosforilo substituidos respectivamente, en caso dado, por flúor, por cloro, por metoxi o por etoxi, significa propenilo, butenilo, propeniloxi, buteniloxi, propenilamino, butenilamino, propilidenamino, butilidenamino, propeniloxicarbonilo, buteniloxicarbonilo, propinilo, butinilo, propiniloxi, butiniloxi, propinilamino, butinilamino, propiniloxicarbonilo o butiniloxicarbonilo substituidos respectivamente, en caso dado, por flúor o por cloro, ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropiloxi, ciclobutiloxi, ciclopentiloxi, ciclohexiloxi, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo, ciclohexilmetilo, ciclopropilmetoxi, ciclobutilmetoxi, ciclopentilmetoxi, ciclohexilmetoxi, ciclopentilidenamino, ciclohexilidenamino, ciclopentiloxicarbonilo, ciclohexiloxicarbonilo, ciclopentilmetoxicarbonilo o ciclohexilmetoxicarbonilo significa, substituidos respectivamente, en caso dado, por flúor, por cloro, por ciano, por carboxi, por metilo, por etilo, por n- o i-propilo, por metoxicarbonilo o por etoxicarbonilo, o significa fenilo, feniloxi, bencilo, feniletilo, benciloxi, feniloxicarbonilo, benciloxicarbonilo, substituidos respectivamente, en caso dado, por nitro, por ciano, por carboxi, por flúor, por cloro, por bromo, por metilo, por etilo, por n- o i-propilo, por triflúormetilo, por metoxi, por etoxi, por n- o i-propoxi, por diflúormetoxi, por triflúormetoxi, por metoxicarbonilo y/o por etoxicarbonilo, pirrolilo, pirazolilo, imidazolilo, triazolilo, furilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, oxadiazolilo, tiadiazolilo, piridinilo, pirimidinilo, triazinilo, pirazolilmetilo, furilmetilo, tienilmetilo, oxazolilmetilo, isoxazolmetilo, tiazolmetilo, piridinilmetilo, pirimidinilmetilo, pirazolmetoxi, furilmetoxi o piridilmetoxi, (hidrogenados en caso dado respectivamente total o parcialmente)means hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, means, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i- s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- o i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- o i-propylamino, n-, i-, s- o t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- o i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl respectively substituted, if necessary, by fluorine, by chlorine, by methoxy or by ethoxy, it means propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenamino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butyloxy, propylamino, butylamino, propynyloxycarbonyl or butynyloxycarbonyl respectively substituted, if necessary, by fluorine or chlorine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl means, substituted respectively, if necessary, by fluorine, by chlorine, by cyano, by carboxy, by methyl, for ethyl, for n- or i-propyl, for methoxycarbonyl or ethoxycarbonyl, or means phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, substituted respectively, where appropriate, by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by methyl, for ethyl, for n- or i-propyl, for trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by difluoromethoxy, by trifluoromethoxy, by methoxycarbonyl and / or by ethoxycarbonyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolmethoxy, furylmethoxy or pyridylmethoxy, (hydrogenated if appropriate respectively total or partially)

R^{3}R 3
significa hidrógeno, flúor o cloro.means hydrogen, fluorine or chlorine.

Las definiciones de los restos indicadas anteriormente de manera general o en los intervalos preferentes son válidas tanto para los productos finales de la fórmula (I) como también, de manera correspondiente, para los productos de partida o bien los productos intermedios necesarios respectivamente para la obtención. Estas definiciones de los restos pueden combinarse arbitrariamente entre sí, es decir por lo tanto también entre los intervalos indicados de los compuestos preferentes.The definitions of the indicated remains previously in general or at the preferred intervals are valid for both the final products of formula (I) and also, correspondingly, for the starting products or well the intermediate products necessary respectively for the obtaining. These definitions of the remains can be combined arbitrarily with each other, that is therefore also among the indicated ranges of preferred compounds.

Ejemplos de los compuestos según la invención de la fórmula (I) se han indicado en los grupos siguientes.Examples of the compounds according to the invention of Formula (I) has been indicated in the following groups.

Grupo 1Group one 

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip
    

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip

44 

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip

R^{1}, R^{2} y R^{3} 

\;
tienen en este caso los significados indicados en el listado siguiente:R 1, R 2 and R 3 
 \;
in this case they have the meanings indicated in the following list: 

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip
    

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip
    

       \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip

(Tabla pasa a página siguiente)(Table goes to page next)

55

66

77

Grupo 2Group 2

88

Si se emplean por ejemplo la 2-(2-flúor-4-ciano-5-metoxi-fenil)-4-metil-5-diflúormetil-2,4-dihidro-3H-1,2,4-triazol-3-ona y sulfuro de hidrógeno como productos de partida, podrá esquematizarse el desarrollo de la reacción del procedimiento según la invención por medio del esquema de fórmulas siguiente:If they are used for example the 2- (2-Fluoro-4-cyano-5-methoxy-phenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one and hydrogen sulfide as starting products, may Outline the development of the process reaction according to the invention by means of the following formula scheme:

99

Los nitrilos aromáticos substituidos a ser empleados como productos de partida en el procedimiento según la invención para la obtención de los compuestos de la fórmula general (I), están definidos, en general, por medio de la fórmula (II). En la fórmula (II) R^{1}, R^{2}, R^{3} y Z tienen preferentemente o bien especialmente aquellos significados que ya han sido citados preferentemente o bien de forma especialmente preferente para R^{1}, R^{2}, R^{3} y Z anteriormente en relación con la descripción de los compuestos de la fórmula (I).The aromatic nitriles substituted to be used as starting products in the procedure according to the invention for obtaining the compounds of the general formula (I), are defined, in general, by the formula (II). In Formula (II) R 1, R 2, R 3 and Z preferably have or especially those meanings that have already been cited preferably or especially preferably for R1, R2, R3 and Z above in relation to the description of the compounds of the formula (I).

Los productos de partida de la fórmula (II) son conocidos y/o pueden prepararse según procedimientos conocidos (véanse las EP-A 370332; DE-A 4238125; DE-A 4303376; US-P 5084084; ejemplos de obtención).The starting products of the formula (II) are known and / or can be prepared according to known procedures (see EP-A 370332; DE-A 4238125; DE-A 4303376; US-P 5084084; obtaining examples).

Como diluyentes para la realización del procedimiento según la invención entran en consideración los disolventes orgánicos usuales. A éstos pertenecen especial-mente hidrocarburos alifáticos, alicíclicos o aromáticos, en caso dado halogenados, tales como por ejemplo bencina, benceno, tolueno, xileno, clorobenceno, diclorobenceno, éter de petróleo, hexano, ciclohexano, diclorometano, cloroformo, tetraclorometano; éteres, tales como dietiléter, diisopropiléter, dioxano, tetrahidrofurano o etilenglicoldimetil- o -dietiléter; cetonas tales como acetona, butanona o metil-isobutil-cetona; nitrilos, tales como acetonitrilo, propionitrilo o benzonitrilo; amidas, tales como N,N-dimetilformamida, N,N-dimetilacetamida, N-metilformanilida, N-metil-pirrolidona o hexametilfósforotriamida; ésteres tales como acetato de metilo o acetato de etilo, sulfóxidos, tal como dimetilsulfóxido, azinas, tal como piridina, alcoholes tales como metanol, etanol, n- o i-propanol, etilenglicolmonometiléter, etilenglicolmonoetiléter, dietilenglicolmonometiléter, dietilenglicolmonoetiléter, sus mezclas con agua o agua pura.As diluents for the realization of procedure according to the invention the usual organic solvents. To these belong especially aliphatic, alicyclic hydrocarbons or aromatic, if appropriate halogenated, such as for example benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachloromethane; ethers, such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran or ethylene glycol dimethyl- or -diethyl ether; ketones such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or benzonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone or hexamethyl phosphorotriamide; esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethylsulfoxide, azines, such such as pyridine, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures with water or pure water.

El procedimiento según la invención se lleva a cabo preferentemente en presencia de un agente auxiliar de la reacción adecuado. Como tales entran en consideración todas las bases inorgánicas u orgánicas usuales. A éstas pertenecen por ejemplo hidruros, hidróxidos, amidas, alcoholatos, acetatos, carbonatos, o bicarbonatos de metales alcalinos o de metales alcalinotérreos, tales como por ejemplo hidruro de sodio, amida de sodio, metilato de sodio, etilato de sodio, terc.-butilato de potasio, hidróxido de sodio, hidróxido de potasio, hidróxido de amonio, acetato de sodio, acetato de potasio, acetato de calcio, acetato de amonio, carbonato de sodio, carbonato de potasio, bicarbonato de potasio, bicarbonato de sodio o carbonato de amonio, así como compuestos nitrogenados orgánicos básicos tales como trimetilamina, trietilamina, tributilamina, N,N-dimetilanilina, piridina, N-metilpiperidina, N,N-dimetilaminopiridina, diazabiciclooctano (DABCO), diazabiciclononeno (DBN) o diazabicicloundeceno (DBU).The process according to the invention is carried out preferably carried out in the presence of an auxiliary agent of the adequate reaction. As such, all the usual inorganic or organic bases. To these belong by example hydrides, hydroxides, amides, alcoholates, acetates, carbonates, or alkali metal or metal bicarbonates alkaline earth metals, such as for example sodium hydride, amide sodium, sodium methylate, sodium ethylate, tert-butylate potassium, sodium hydroxide, potassium hydroxide, hydroxide ammonium, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, as well as basic organic nitrogen compounds such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

Las temperaturas de la reacción pueden variar dentro de amplios límites en la realización del procedimiento según la invención. En general se trabaja a temperaturas comprendidas entre 0ºC y 100ºC, preferentemente a temperaturas comprendidas entre 10ºC y 80ºC.Reaction temperatures may vary. within wide limits in performing the procedure according to the invention. In general it works at temperatures included between 0 ° C and 100 ° C, preferably at temperatures between 10ºC and 80ºC.

El procedimiento según la invención se lleva a cabo en general bajo presión normal. No obstante es posible también trabajar bajo presión más elevada o a presión más reducida -en general entre 0,1 bares y 10 bares-.The process according to the invention is carried out out in general under normal pressure. However it is also possible work under higher pressure or lower pressure -in general between 0.1 bars and 10 bars.

Para la realización del procedimiento según la invención se disponen los productos de partida de la fórmula (II) en general en un diluyente adecuado en presencia de un agente auxiliar de la reacción y se dosifica lentamente el sulfuro de hidrógeno o la tioacetamida. Preferentemente se emplearán el sulfuro de hidrógeno o la tioacetamida en un gran exceso. La mezcla de la reacción se agita durante varias horas a la temperatura necesaria en cada caso. La elaboración se lleva a cabo en el procedimiento según la invención respectivamente según métodos usuales (véanse los ejemplos de obtención).To perform the procedure according to the invention the starting products of the formula (II) are arranged in general in a suitable diluent in the presence of an auxiliary agent of the reaction and the hydrogen sulfide or the thioacetamide. Preferably hydrogen sulfide or Thioacetamide in a large excess. The reaction mixture is stirred. for several hours at the necessary temperature in each case. The processing is carried out in the process according to the invention respectively according to usual methods (see examples of obtaining).

Los productos activos según la invención se pueden emplear como defoliantes, desecantes, agentes herbicidas y especialmente como agentes para eliminar las malas hierbas. Por malas hierbas, en el más amplio sentido, se han de entender las plantas que crecen en lugares donde son indeseadas. El hecho de que las substancias, según la invención, actúen como herbicidas totales o selectivos, depende esencialmente de la cantidad empleada.The active products according to the invention are they can use as defoliant, desiccants, herbicidal agents and especially as agents to eliminate weeds. By weeds, in the broadest sense, the plants that grow in places where they are unwanted. The fact that the substances, according to the invention, act as total herbicides or selective, depends essentially on the amount used.

Los productos activos, según la invención se pueden emplear, por ejemplo, en las plantas siguientes:The active products according to the invention are they can be used, for example, in the following plants:

Hierbas malas dicotiledóneas de las clases: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus Portulaca, Xanthium, Convolvulus, Impomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Geleopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicotyledonous weeds of the classes : Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus Portulaca, Xanthium, Convolvulus, Impomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sondulan, Sondulan, Soduum, Sondulan, Soduum Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Geleopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum .

Cultivos de dicotiledóneas de las clases: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon,Arachis , Bassica, Lactuca, Cucumis, Cucurbita. Cultures of dicotyledons of the classes : Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Bassica, Lactuca, Cucumis, Cucurbita .

Hierbas malas monocotiledóneas de las clases: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrotis, Alopecurus, Apera. Monocotyledonous weeds of the classes : Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharisum Sopus, Paso , Ischaemum, Sphenoclea, Dactyloctenium, Agrotis, Alopecurus, Apera .

Cultivos de monocotiledóneas de las clases: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium. Crops of monocots of the classes : Oryza, Zea, Triticum, Hordeum, Oatmeal, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium .

El empleo de los productos activos según la invención, no está sin embargo, limitado en forma alguna a estas clases, sino que se extiende en igual forma también sobre otras plantas.The use of active products according to the invention, however, is not limited in any way to these classes, but also extends equally over other plants.

Los compuestos son adecuados, en función de la concentración, para combatir totalmente las hierbas malas, por ejemplo, en instalaciones industriales y viarias y en caminos y plazas, con y sin crecimiento de árboles. Del mismo modo, se pueden emplear los compuestos para combatir las hierbas malas en cultivos permanentes, por ejemplo, en instalaciones forestales, de árboles de adorno, de árboles frutales, de viñedos, de árboles cítricos, de nogales, de plátanos, de café, de té, de goma de palmas de aceite, de cacao, de frutos de bayas y de lúpulo, en prados ornamentales y deportivos y en superficies de praderas y para combatir las hierbas malas en forma selectiva en los cultivos mono-anuales.The compounds are suitable, depending on the concentration, to totally combat weeds, by for example, in industrial and road installations and on roads and squares, with and without tree growth. Similarly, you can use compounds to combat weeds in crops permanent, for example, in forest facilities, of trees ornament, fruit trees, vineyards, citrus trees, walnuts, bananas, coffee, tea, rubber palm oil, of cocoa, berries and hops, in ornamental meadows and sports and on grassland surfaces and to combat herbs badly selectively in crops mono-annual

Los compuestos de la fórmula (I) según la invención son adecuados especialmente para la lucha selectiva contra las malas hierbas monocotiledóneas y dicotiledóneas en cultivos monocotiledóneos y dicotiledóneos, tanto en procedimientos de pre-brote como en procedimientos de post-brote.The compounds of the formula (I) according to the invention are especially suitable for the selective fight against monocotyledonous and dicotyledonous weeds in crops monocotyledonous and dicotyledonous, both in procedures pre-outbreak as in procedures post-outbreak

En cierta medida los compuestos de la fórmula (I) muestran también efecto fungicida, por ejemplo contra Pyricularia oryzae en el arroz.To some extent the compounds of the formula (I) also show a fungicidal effect, for example against Pyricularia oryzae in rice.

Los productos activos se pueden transformar en las formulaciones usuales, tales como soluciones, emulsiones, polvos pulverizables, suspensiones, polvos, medios de espolvoreo, pastas, polvos solubles, granulados, concentrados de suspensión-emulsión, materiales naturales y sintéticos impregnados con el producto activo, así como microencapsulados en materiales polímeros.Active products can be transformed into usual formulations, such as solutions, emulsions, powders sprays, suspensions, powders, dusting media, pastes, soluble, granulated, concentrated powders of suspension-emulsion, natural materials and synthetic impregnated with the active product, as well as microencapsulated in polymeric materials.

Estas formulaciones se preparan en forma conocida, por ejemplo, mediante mezcla de los productos activos con materiales extendedores, esto es, con disolventes líquidos y/o excipientes sólidos, en caso dado, empleando agentes tensioactivos, esto es, emulsionantes y/o dispersantes y/o medios generadores de espuma.These formulations are prepared in the form known, for example, by mixing the active products with spreading materials, that is, with liquid solvents and / or solid excipients, if appropriate, using surfactants, that is, emulsifiers and / or dispersants and / or generating means of foam.

En el caso de emplear agua como material de carga se puede emplear, por ejemplo, también disolventes orgánicos como agentes disolventes auxiliares. Como disolventes líquidos entran especialmente en consideración: los hidrocarburos aromáticos, tales como xileno, tolueno, o alquilnaftalenos, los hidrocarburos aromáticos clorados y los hidrocarburos alifáticos clorados, tales como los clorobencenos, cloroetilenos o cloruro de metileno, los hidrocarburos alifáticos, tales como ciclohexano o las parafinas, por ejemplo, las fracciones de petróleo crudo, los aceites minerales y vegetales, los alcoholes, tales como butanol, o glicol, así como sus ésteres y éteres, las cetonas, tales como acetona, metiletilcetona, metilisobutilcetona, o ciclohexanona, los disolventes fuertemente polares, tales como dimetilformamida y dimetilsulfóxido, así como el agua.In the case of using water as a loading material for example, organic solvents such as auxiliary solvent agents. How liquid solvents enter especially in consideration: aromatic hydrocarbons, such such as xylene, toluene, or alkylnaphthalenes, hydrocarbons chlorinated aromatics and chlorinated aliphatic hydrocarbons, such such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example, fractions of crude oil, mineral oils and vegetables, alcohols, such as butanol, or glycol, as well as its esters and ethers, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, as well as water.

Como excipientes sólidos entran en consideración:How solid excipients enter consideration:

por ejemplo, sales de amonio y los minerales naturales molturados, tales como caolines, arcillas, talco, creta, cuarzo, atapulgita, montmorillonita o tierra de diatomeas y minerales sintéticos molturados, tales como ácido silícico, altamente disperso, óxido de aluminio y silicatos como excipientes sólidos para granulados entran en consideración: por ejemplo, minerales naturales quebrados y fraccionados tales como calcita, mármol, piedra pómez, sepiolita, dolomita, así como granulados sintéticos de harinas inorgánicas y orgánicas, así como granulados de materiales orgánicos, tales como serrines, cáscaras de nuez de coco, panochas de maíz y tallos de tabaco; como emulsionantes y/o generadores de espuma entran en consideración por ejemplo, los emulsionantes no ionógenos y aniónicos, tales como ésteres polioxietilenados de ácidos grasos, por ejemplo, alquilarilpoliglicoléter, alquilsulfonatos, alquilsulfatos, arilsulfonatos, así como los hidrolizados de albúmina; como dispersantes entran en consideración, por ejemplo, lixiviaciones sulfíticas de lignina y metilcelulosa.for example, ammonium salts and minerals natural milled, such as kaolins, clays, talc, crete, quartz, attapulgite, montmorillonite or diatomaceous earth and milled synthetic minerals, such as silicic acid, highly dispersed, aluminum oxide and silicates as excipients solids for granules come into consideration: for example, broken and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, as well as granules Synthetic inorganic and organic flours, as well as granules of organic materials, such as sawdust, nutshells from coconut, corn husks and tobacco stalks; as emulsifiers and / or foam generators come into consideration for example the non-ionic and anionic emulsifiers, such as esters polyoxyethylene fatty acids, for example, alkylaryl polyglycol ether, alkylsulfonates, alkylsulfates, arylsulfonates, as well as albumin hydrolysates; how dispersants come into consideration, for example, leaching sulphites of lignin and methylcellulose.

En las formulaciones se pueden emplear adhesivos tales como carboximetilcelulosa, polímeros naturales y sintéticos pulverulentos, granulados o en forma de látex, tales como goma arábiga, alcohol polivinílico, acetato de polivinilo, así como fosfolípidos naturales, tales como cefalina y lecitina, y fosfolípidos sintéticos. Otros aditivos pueden ser aceites minerales y vegetales.In the formulations adhesives can be used such as carboxymethyl cellulose, natural and synthetic polymers powder, granules or latex, such as rubber Arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids Other additives may be mineral oils and vegetables

Se pueden emplear colorantes, tales como pigmentos inorgánicos, por ejemplo, óxido de hierro óxido de titanio, azul ferrociánico y colorantes orgánicos, tales como colorantes de alizarina, colorantes azoicos y de ftalocianina metálicos y nutrientes en trazas, tales como sales de hierro, manganeso, boro, cobre, cobalto, molibdeno y cinc.Dyes, such as inorganic pigments, for example, iron oxide oxide titanium, ferrocyanic blue and organic dyes, such as alizarin dyes, azo dyes and phthalocyanine dyes metallic and trace nutrients, such as iron salts, manganese, boron, copper, cobalt, molybdenum and zinc.

Las formulaciones contienen, por lo general, entre un 0,1 hasta un 95% en peso de producto activo, preferentemente entre un 0,5 y un 90%.The formulations generally contain between 0.1 to 95% by weight of active product, preferably between 0.5 and 90%.

Los productos activos, según la invención, pueden emplearse como tales o en sus formulaciones también para la lucha contra las malas hierbas en mezcla con herbicidas siendo posibles preparados listos para su empleo o mezclas de tanque.The active products according to the invention can be used as such or in its formulations also for the fight against weeds in mixture with herbicides being possible ready-to-use preparations or tank mixtures.

Para las mezclas entran en consideración herbicidas conocidos tales como por ejemplo, Diflufenican y Propanil; ácidos arilcarboxílicos, tales como, por ejemplo, ácido dicloropicolínico, Dicamba y Picloram; ácidos ariloxialcanoicos, tales como, por ejemplo, 2,4 D, 2,4 DB, 2,4 DP, Fluroxypyr, MCPA, MCPP y Triclopyr; ésteres de ácidos ariloxi-fenoxi-alcanoicos, tales como, por ejemplo, Diclofop (-metilo), Fenoxaprop (-etilo), Fluazifop (-butilo), Haloxyfop (-metilo) y Quizalofop (-etilo); Azinone, tales como, por ejemplo, Chloridazon y Norflurazon; Carbamate, tales como, por ejemplo, Chlorpropham, Desmedipham, Phenmedipham y Propham; cloroacetanilidas, tales como, por ejemplo, Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor y Propachlor; dinitroanilinas, tales como, por ejemplo, Oryzalin, Pendimethalin y Trifluralin; difeniléteres, tales como, por ejemplo, Acifluorfen, Bifenox, Chlormethoxynil (X-52), Chlomitrofen, Fluoroglycofen, Fomesafen, Halosafen, Lactofen, Nitrofen y Oxyfluorfen; ureas, tales como, por ejemplo, Chlortoluron, Cumyluron (JC-940), Diuron, Dymron (Daimuron), Fluometuron, Isoproturon, Linuron y Methabenzthiazuron; hidroxilaminas, tales como, por ejemplo, Alloxydim, Clethodim, Cycloxydim, Sethoxydim y Tralkoxydim; imidazolinonas, tales como, por ejemplo, Imazethapyr, Imazamethabenz, Imazapyr y Imazaquin; nitrilos, tales como, por ejemplo, Bromoxynil, Dichlobenil y Ioxynil; oxiacetamidas, tal como, por ejemplo, Mefenacet; sulfonilureas, tales como, por ejemplo, AC-014 (AC-322140), Amidosulfuron, Bensulfuron (-metilo), Chlorimuron (-etilo), Chlorsulfuron, Cinosulfuron, DPX-47, HOE-404, Imazosulfuron, Metsulfuron (-metilo), Nicosulfuron, Primisulfuron, Pyrazosulfuron (-etilo), Thifensulfuron (-metilo), Triasulfuron y Tribenuron (-metilo); tiolcarbamatos, tales como, por ejemplo, Butylate, Cycloate, Diallate, Dimepiperate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb (Benthiocarb) y Triallate; triazinas, tales como, por ejemplo, Atrazin, Cyanazin, Dimethametryn, Prometryne, Simazin, Simetryne, Terbutryne y Terbutylazin; triazinonas, tales como, por ejemplo, Hexazinon, Metamitron y Metribuzin; otros, tales como, por ejemplo, Aminotriazol, Benfuresate, Bensulide, Bentazone, Benzofenap, Bromobutide, Butamifos, Cafenstrole (CH-900), Cinmethylin, Clomazone, Clomeprop, Clopyralid, DEH-112, Difenzoquat, Dimethenamid, Dithiopyr, Ethofumesate, Flumetsulam, Fluorochloridone, Glufosinate, Glyphosate, Amiprophos (-metilo), Anilofos, Etobenzanid (HW-52), Isoxaben, KPP-314, KUH-833, KUH-911, KUH-920, MK-243, Naproanilide, NSK-850, Oxadiazon, Piperophos, Propanil, Pyrazolate, Pyrazoxyfen, Pyributicarb, Pyridate, Quinchlorac, Quinmerac, Sulphosate y Tridiphane.For mixtures come into consideration known herbicides such as, for example, Diflufenican and Propanil; arylcarboxylic acids, such as, for example, acid dichloropicolinic, Dicamba and Picloram; aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP, Fluroxypyr, MCPA, MCPP and Triclopyr; acid esters aryloxy-phenoxy-alkanoic acids, such such as Diclofop (-methyl), Phenoxaprop (-ethyl), Fluazifop (-butyl), Haloxyfop (-methyl) and Quizalofop (-ethyl); Azinone, such as, for example, Chloridazon and Norflurazon; Carbamate, such as, for example, Chlorpropham, Desmedipham, Phenmedipham and Propham; chloroacetanilides, such as, for example, Alachlor, Acetochlor, Butachlor, Metazachlor, Metolachlor, Pretilachlor and Propachlor; dinitroanilines, such as, for example, Oryzalin, Pendimethalin and Trifluralin; diphenyl ethers, such as, for example, Acifluorfen, Bifenox, Chlormethoxynil (X-52), Chlomitrofen, Fluoroglycofen, Fomesafen, Halosafen, Lactofen, Nitrofen and Oxyfluorfen; ureas, such as, by example, Chlortoluron, Cumyluron (JC-940), Diuron, Dymron (Daimuron), Fluometuron, Isoproturon, Linuron and Methabenzthiazuron; hydroxylamines, such as, for example, Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; imidazolinones, such as, for example, Imazethapyr, Imazamethabenz, Imazapyr and Imazaquin; nitriles, such as, by example, Bromoxynil, Dichlobenil and Ioxynil; oxyacetamides, such as, for example, Mefenacet; sulfonylureas, such as, for example, AC-014 (AC-322140), Amidosulfuron, Bensulfuron (-methyl), Chlorimuron (-ethyl), Chlorsulfuron, Cinosulfuron, DPX-47, HOE-404, Imazosulfuron, Metsulfuron (-methyl), Nicosulfuron, Primisulfuron, Pyrazosulfuron (-ethyl), Thifensulfuron (-methyl), Triasulfuron and Tribenuron (-methyl); thiolcarbamates, such as, for example, Butylate, Cycloate, Diallate, Dimepiperate, EPTC, Esprocarb, Molinate, Prosulfocarb, Thiobencarb (Benthiocarb) and Triallate; triazines, such as, for example, Atrazin, Cyanazin, Dimethametryn, Prometryne, Simazin, Simetryne, Terbutryne and Terbutylazin; triazinones, such as, for example, Hexazinon, Metamitron and Metribuzin; others, such as, for example, Aminotriazole, Benfuresate, Bensulide, Bentazone, Benzofenap, Bromobutide, Butamifos, Cafenstrole (CH-900), Cinmethylin, Clomazone, Clomeprop, Clopyralid, DEH-112, Difenzoquat, Dimethenamid, Dithiopyr, Ethofumesate, Flumetsulam, Fluorochloridone, Glufosinate, Glyphosate, Amiprophos (-methyl), Anilofos, Etobenzanid (HW-52), Isoxaben, KPP-314, KUH-833, KUH-911, KUH-920, MK-243, Naproanilide, NSK-850, Oxadiazon, Piperophos, Propanil, Pyrazolate, Pyrazoxyfen, Pyributicarb, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.

También es posible una mezcla con otros productos activos conocidos, tales como fungicidas, insecticidas, acaricidas, nematicidas, substancias protectoras contra la ingestión por pájaros, substancias nutrientes de las plantas y medios mejoradores de la estructura del terreno.It is also possible to mix with other products known assets, such as fungicides, insecticides, acaricides, nematicides, protective substances against ingestion by birds, plant nutrients and breeding media of the structure of the land.

Los productos activos pueden emplearse como tales, en forma de sus formulaciones o de las formas de aplicación preparadas a partir de las mismas mediante diluciones ulteriores, tales como soluciones listas para su empleo, suspensiones, emulsiones, polvos, pastas y granulados. El empleo se lleva a cabo en forma usual por ejemplo mediante riego, pulverización, aspersión, esparcido.Active products can be used as such, in the form of its formulations or the forms of application prepared therefrom by further dilutions, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. The employment is carried out in the usual way for example by irrigation, spraying, spraying, scattered.

Los productos activos según la invención pueden aplicarse tanto antes como después del brote de las plantas. También pueden incorporarse, en el suelo antes de la siembra.The active products according to the invention can apply both before and after the plant sprout. Too They can be incorporated into the soil before planting.

Las cantidades de producto activo empleados pueden oscilar dentro de un amplio margen. Estas dependen fundamentalmente del tipo del efecto deseado. En general las cantidades empleadas se sitúan entre 10 g y 10 kg de producto activo por hectárea de superficie del terreno, preferentemente entre 50 g y 5 kg por hectárea.The quantities of active product used They can oscillate within a wide range. These depend fundamentally of the type of the desired effect. In general the quantities used are between 10 g and 10 kg of active product per hectare of land area, preferably between 50 g and 5 kg per hectare.

La obtención y el empleo de los productos activos según la invención se deduce de los ejemplos siguientes:Obtaining and using active products according to the invention it follows from the following examples:

Ejemplos de obtenciónExamples of obtaining Ejemplo 1Example 1

1010

Se combinan 6,3 g (0,02 moles) de la 2-(2-flúor-4-ciano-5-amino-fenil)-4-etil-5-triflúormetil-2,4-dihidro-3H-1,2,4-triazol-3-ona en 100 ml de acetona con 4,04 g (0,04 moles) de trietilamina. Se borbotea ahora, a 23ºC, rápidamente, sulfuro de hidrógeno, con lo que la temperatura interna se eleva hasta 33ºC. Al cabo de una hora la reacción es completa. La solución se concentra por evaporación en el evaporador rotativo y el residuo se recristaliza en isopropanol.6.3 g (0.02 mol) of the 2- (2-Fluoro-4-cyano-5-amino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 100 ml of acetone with 4.04 g (0.04 mol) of triethylamine. Be now, at 23 ° C, rapidly, hydrogen sulfide, so that the internal temperature rises to 33 ° C. After one hour The reaction is complete. The solution is concentrated by evaporation in the rotary evaporator and the residue is recrystallized in isopropanol

Se obtienen 2,9 g (42% de la teoría) de la 2-(2-flúor-4-tiocarbamoil-5-amino-fenil)-4-etil-5-triflúormetil-2,4-dihidro-3H-1,2,4-triazol-3-ona con un punto de fusión de 161ºC.2.9 g (42% of theory) of the 2- (2-Fluoro-4-thiocarbamoyl-5-amino-phenyl) -4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one with a melting point of 161 ° C.

Ejemplo 2Example 2

11eleven

Se agitan 11 g (0,0276 moles) de la 2-(2-flúor-4-ciano-5-etilsulfonilaminofenil)-4-metil-5-diflúormetil-2,4-dihidro-3H-1,2,4-triazol-3-tiona en 100 ml de piridina con borboteo de sulfuro de hidrógeno durante 4,5 horas a 70ºC. La solución se concentra por evaporación en el evaporador rotativo, el residuo se agita con agua, se acidifica con ácido clorhídrico concentrado, el producto precipitado se separa por filtración, se lava con agua y se recristaliza en isopropanol.11 g (0.0276 mol) of the 2- (2-Fluoro-4-cyano-5-ethylsulfonylaminophenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-thione in 100 ml of pyridine with hydrogen sulfide bubbling during 4.5 hours at 70 ° C. The solution is concentrated by evaporation in the rotary evaporator, the residue is stirred with water, acidified with concentrated hydrochloric acid, the precipitated product is separated by filtration, washed with water and recrystallized from isopropanol.

Se obtienen 9 g (77% de la teoría) de la 2-(2-flúor-4-tiocarbamoil-5-etilsulfonilaminofenil)-4-metil-5-diflúormetil-2,4-dihidro-3H-1,2,4-triazol-3-tiona con un punto de fusión de 183ºC.9 g (77% of theory) of the 2- (2-Fluoro-4-thiocarbamoyl-5-ethylsulfonylaminophenyl) -4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-thione with a melting point of 183 ° C.

De manera análoga a la de los ejemplos de obtención 1 y 2 así como de acuerdo con la descripción general del procedimiento de obtención según la invención pueden prepararse por ejemplo también los compuestos de la fórmula (I) indicados en la tabla 1 siguiente.Similarly to the examples of obtaining 1 and 2 as well as in accordance with the general description of the method of obtaining according to the invention can be prepared by example also the compounds of the formula (I) indicated in the table 1 below.

1212

TABLA 1TABLE 1 Ejemplos de compuestos de la fórmula (I)Examples of compounds of the formula (I)

1313

1414

15fifteen

Obtención de los compuestos de partidaObtaining the starting compounds

Ejemplo II-1Example II-1

1717

Se agregan a 6,3 g (0,034 moles) de 4-metil-3-triflúormetil-1,2,4-triazolin-5-ona (véase por ejemplo la publicación US 3.780.052) y 5,4 g (0,034 moles) de 2,4,5-triflúorbenzonitrilo (véase por ejemplo la publicación EP 191181) en 150 ml de dimetilsulfóxido, a temperatura ambiente, 5,8 g (0,042 moles) de carbonato de potasio y se calienta a continuación durante 14 horas a 100ºC. Para la elaboración se vierte la mezcla de la reacción enfriada en agua, se lleva a pH 2 con ácido clorhídrico diluido y se extrae varias veces con diclorometano. Las fases orgánicas reunidas se secan sobre sulfato de sodio y se concentran por evaporación en vacío. El residuo se cromatografía a través de gel de sílice (eluyente: diclorometano).They are added to 6.3 g (0.034 mol) of 4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one (see for example US publication 3,780,052) and 5.4 g (0.034 moles) of 2,4,5-trifluorobenzonitrile (see for Example EP 191181) in 150 ml of dimethylsulfoxide, a room temperature, 5.8 g (0.042 mol) of potassium carbonate and it is then heated for 14 hours at 100 ° C. For the elaboration the mixture of the reaction cooled in water is poured, it takes to pH 2 with diluted hydrochloric acid and is extracted several times with dichloromethane. The combined organic phases are dried over sodium sulfate and concentrated by evaporation in vacuo. He residue is chromatographed through silica gel (eluent: dichloromethane).

Se obtienen 6,2 g (60% de la teoría) de la 1-(4-ciano-2,5-diflúorfenil)-4-metil-3-triflúormetil-1,2,4-triazolin-5-ona con un punto de fusión de 74ºC.6.2 g (60% of theory) of the 1- (4-Cyano-2,5-difluorphenyl) -4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one with a melting point of 74 ° C.

Ejemplo II-2Example II-2

1818

Se agregan a 1,52 g (0,005 moles) de 1-(4-ciano-2,5-diflúorfenil)-4-metil-3-triflúormetil-1,2,4-triazolin-5-ona y 0,48 g (0,005 moles) de metanosulfonamida en 50 ml de dimetilsulfóxido a temperatura ambiente, 0,83 g (0,006 moles) de carbonato de potasio y se calienta a continuación durante 12 horas a 120ºC. Para la elaboración se vierte la mezcla de la reacción enfriada en agua, se lleva a pH 2 con ácido clorhídrico diluido y se extrae varias veces con diclorometano. Las fases orgánicas reunidas se secan sobre sulfato de sodio y se concentran por evaporación en vacío. El residuo se cromatografía a través de gel de sílice (eluyente: diclorometano/metanol 20:1).They are added to 1.52 g (0.005 mol) of 1- (4-Cyano-2,5-difluorphenyl) -4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one and 0.48 g (0.005 mol) of methanesulfonamide in 50 ml of dimethylsulfoxide at room temperature, 0.83 g (0.006 mol) of potassium carbonate and then heated for 12 hours at 120 ° C. For the reaction the reaction mixture is poured cooled in water, it is brought to pH 2 with dilute hydrochloric acid and it is extract several times with dichloromethane. The organic phases gathered they are dried over sodium sulfate and concentrated by evaporation in empty. The residue is chromatographed through silica gel. (eluent: dichloromethane / methanol 20: 1).

Se obtienen 0,55 g (28% de la teoría) de 1-(4-ciano-2-flúor-5-metilsulfonilaminofenil)-4-metil-3-triflúormetil-1,2,4-triazolin-5-ona con un punto de fusión de 67ºC.0.55 g (28% of theory) of 1- (4-Cyano-2-fluorine-5-methylsulfonylaminophenyl) -4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one with a melting point of 67 ° C.

1919

Ejemplo BExample B Ensayo de post-brotePost-outbreak test

Disolvente:Solvent: 5 Partes en peso de acetona5 Parts by weight of acetone Emulsionante:Emulsifier: 1 Parte en peso de alquilarilpoliglicoléter.1 Part by weight of alkylaryl polyglycol ether.

Para la obtención de una preparación conveniente de producto activo, se mezcla 1 parte en peso de producto activo con la cantidad indicada de disolvente, se agrega la cantidad indicada de emulsionante y el concentrado se diluye con agua hasta la concentración deseada.To obtain a convenient preparation of active product, 1 part by weight of active product is mixed with the indicated amount of solvent, the indicated amount is added of emulsifier and the concentrate is diluted with water until desired concentration

Se pulverizan plantas de ensayo, que tienen una altura de 5 hasta 15 cm, con la preparación del producto activo de manera, que en cada caso, se apliquen las cantidades de producto activo deseadas por unidad de superficie. Al cabo de tres semanas se evalúa el grado de daños de las plantas en% de daños en comparación con el desarrollo del control sin tratar.Test plants are sprayed, which have a height from 5 to 15 cm, with the preparation of the active product of way, that in each case, the quantities of product are applied desired assets per unit area. After three weeks you assesses the degree of damage of plants in% of damage compared with the development of untreated control.

Significan:They mean:

0%0% == ningún efecto (como los controles no tratados).no effect (as controls do not treated). 100%100% == destrucción total.destruction total. 

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(Tabla pasa a página siguiente)(Table goes to page next)

20twenty

Claims (8)

1. Amidas substituidas de ácidos tiocarboxílicos, aromáticas, de la fórmula general (I)1. Substituted amides of thiocarboxylic acids, aromatic, of the general formula (I) 21twenty-one en la quein the that
R^{1}R1
significa hidrógeno, flúor, cloro o bromo,means hydrogen, fluorine, chlorine or bromine,
R^{2}R2
significa el agrupamiento siguiente,means the following grouping,
\quadquad
-A^{1}-A^{3}-A 1 -A 3
A^{1}A1
significa oxígeno, azufre o el agrupamiento -N-A^{4}-, donde A^{4} significa hidrógeno, alquilo con 1 a 4 átomos de carbono, alcoxi con 1 a 4 átomos de carbono o alquilsulfonilo con 1 a 4 átomos de carbono,means oxygen, sulfur or clustering -N-A 4 -, where A 4 means hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 atoms of carbon or alkylsulfonyl with 1 to 4 carbon atoms,
A^{3}A3
significa hidrógeno, hidroxi, amino, ciano, isocianato, tiocianato, nitro, carboxi, carbamoilo, tiocarbamoilo, sulfo, clorosulfonilo, halógeno, significa alquilo, alcoxi, alquiltio, alquilsulfinilo, alquilsulfonilo, alquilamino, dialquilamino, alcoxicarbonilo o dialcoxi(tio)fosforilo con, respectivamente, 1 a 6 átomos de carbono en los grupos alquilo, substituidos respectivamente en caso dado por halógeno o alcoxi con 1 a 4 átomos de carbono, significa alquenilo, alqueniloxi, alquenilamino, alquilidenamino, alqueniloxicarbonilo, alquinilo, alquiniloxi, alquinilamino o alquiniloxicarbonilo con, respectivamente, 2 a 6 átomos de carbono en los grupos alquenilo, alquilideno o alquinilo, substituidos respectivamente, en caso dado, por halógeno, significa, cicloalquilo, cicloalquiloxi, cicloalquilalquilo, cicloalquilalcoxi, cicloalquilidenamino, cicloalquiloxicarbonilo o cicloalquilalcoxicarbonilo con, respectivamente, 3 a 6 átomos de carbono en los grupos cicloalquilo y, en caso dado, 1 a 4 átomos de carbono en los grupos alquilo, substituidos respectivamente, en caso dado, por halógeno, por ciano, por carboxi, por alquilo con 1 a 4 átomos de carbono y/o por alcoxicarbonilo con 1 a 4 átomos de carbono, o significa fenilo, feniloxi, fenil-alquilo con 1 a 4 átomos de carbono, fenil-alcoxi con 1 a 4 átomos de carbono, feniloxicarbonilo o fenil-alcoxicarbonilo con 1 a 4 átomos de carbono, substituidos respectivamente, en caso dado, por nitro, por ciano, por carboxi, por halógeno, por alquilo con 1 a 4 átomos de carbono, halógenoalquilo con 1 a 4 átomos de carbono, por alquiloxi con 1 a 4 átomos de carbono, halógenoalquiloxi con 1 a 4 átomos de carbono y/o alcoxi-carbonilo con 1 a 4 átomos de carbono, pirrolilo, pirazolilo, imidazolilo, triazolilo, furilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, oxadiazolilo, tiadiazolilo, piridinilo, pirimidinilo, triazinilo, pirazolil-alquilo con 1 a 4 átomos de carbono, furil-alquilo con 1 a 4 átomos de carbono, tienil-alquilo con 1 a 4 átomos de carbono, oxazolil-alquilo con 1 a 4 átomos de carbono, isoxazol-alquilo con 1 a 4 átomos de carbono, tiazol-alquilo con 1 a 4 átomos de carbono, piridinil-alquilo con 1 a 4 átomos de carbono, isoxazol-alquilo con 1 a 4 átomos de carbono, tiazol-alquilo con 1 a 4 átomos de carbono, piridinil-alquilo con 1 a 4 átomos de carbono, isoxazol-alquilo con 1 a 4 átomos de carbono, tiazol-alquilo con 1 a 4 átomos de carbono, piridinil-alquilo con 1 a 4 átomos de carbono, pirimidinil-alquilo con 1 a 4 átomos de carbono, pirazolilmetoxi, furilmetoxi (respectivamente hidrogenados en caso dado total o parcialmente), significa perhidropiranilmetoxi o piridilmetoxi,means hydrogen, hydroxy, amino, cyano, isocyanate, thiocyanate, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, halogen, means alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl with, respectively, 1 to 6 carbon atoms in the alkyl groups, substituted respectively if necessary by halogen or alkoxy with 1 to 4 atoms carbon, means alkenyl, alkenyloxy, alkenylamino, alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkylamino or alkynyloxycarbonyl with, respectively, 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, respectively, if necessary, substituted by halogen, it means, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl with, respectively, 3 to 6 atoms of carbon in the cycloalkyl groups and, where appropriate, 1 to 4 atoms of carbon in the alkyl groups, substituted respectively, in case given, by halogen, by cyano, by carboxy, by alkyl with 1 to 4 carbon atoms and / or alkoxycarbonyl with 1 to 4 atoms of carbon, or means phenyl, phenyloxy, phenyl-alkyl with 1 to 4 carbon atoms, phenyl-alkoxy with 1 to 4 carbon atoms, phenyloxycarbonyl or phenyl-alkoxycarbonyl with 1 to 4 carbon atoms, respectively substituted, if necessary, by nitro, by cyano, by carboxy, by halogen, by alkyl with 1 to 4 carbon atoms, halogenalkyl with 1 to 4 carbon atoms, by alkyloxy with 1 to 4 carbon atoms, halogenoalkyloxy with 1 to 4 carbon atoms and / or alkoxycarbonyl with 1 to 4 carbon atoms, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-alkyl with 1 to 4 carbon atoms, furyl-alkyl with 1 to 4 carbon atoms, thienyl-alkyl with 1 to 4 carbon atoms, oxazolyl-alkyl with 1 to 4 carbon atoms, isoxazol-alkyl with 1 to 4 carbon atoms, thiazol-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, isoxazol-alkyl with 1 to 4 carbon atoms, thiazol-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, isoxazol-alkyl with 1 to 4 carbon atoms, thiazol-alkyl with 1 to 4 carbon atoms, pyridinyl-alkyl with 1 to 4 carbon atoms, pyrimidinyl-alkyl with 1 to 4 carbon atoms, pyrazolylmethoxy, furylmethoxy (respectively hydrogenated in case given totally or partially), means perhydropyranylmethoxy or pyridylmethoxy,
R^{3}R 3
significa hidrógeno, flúor, cloro, bromo, ymeans hydrogen, fluorine, chlorine, bromine, Y
ZZ
significa el agrupamiento heterocíclico indicado a continuación,means the heterocyclic grouping indicated to continuation, 
         \vskip1.000000\baselineskip\ vskip1.000000 \ baselineskip
2222 en el queat that
Q^{1}Q1
significa -CO- o -CS-,means -CO- or -CS-,
R^{6}R 6
significa diflúormetilo o triflúormetilo, ymeans diflumoromethyl or trifluoromethyl, Y
R^{7}R 7
significa metilo, etilo, n-o i-propilo o diflúormetilo.means methyl, ethyl, n-o i-propyl or difluoromethyl.
2. Amidas substituidas de ácidos tiocarboxílicos, aromáticas según la reivindicación 1, caracterizadas porque2. Aromatic thiocarboxylic acid substituted amides according to claim 1, characterized in that
R^{1}R1
significa hidrógeno, flúor o cloro,means hydrogen, fluorine or chlorine,
R^{2}R2
significa el agrupamiento siguiente,means the following grouping,
\quadquad
-A^{1}- A^{3}-A 1 - A 3
\quadquad
en el quein which
A^{1}A1
significa oxígeno, azufre o el agrupamiento -N-A^{4}-, donde A^{4} significa hidrógeno, metilo, etilo, n- o i-propilo, metoxi, etoxi, n- o i-propoxi, metilsulfonilo o etilsulfonilo,means oxygen, sulfur or clustering -N-A 4 -, where A 4 means hydrogen, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A^{3}A3
significa hidrógeno, hidroxi, amino, ciano, nitro, carboxi, carbamoilo, sulfo, flúor, cloro, bromo, significa, metilo, etilo, n- o i-propilo, n-, i-, s- o t-butilo, n-, i-, s- o t-pentilo, metoxi, etoxi, n- o i-propoxi, n-, i-, s- o t-butoxi, n-, i-, s- o t-pentiloxi, metiltio, etiltio, n- o i-propiltio, n-, i- s- o t-butiltio, metilsulfinilo, etilsulfinilo, n- o i-propilsulfinilo, metilsulfonilo, etilsulfonilo, n- o i-propilsulfonilo, metilamino, etilamino, n- o i-propilamino, n-, i-, s- o t-butilamino, dimetilamino, dietilamino, metoxicarbonilo, etoxicarbonilo, n- o i-propoxicarbonilo, dimetoxifosforilo, dietoxifosforilo, dipropoxifosforilo o diisopropoxifosforilo substituidos respectivamente, en caso dado, por flúor, por cloro, por metoxi o por etoxi, significa propenilo, butenilo, propeniloxi, buteniloxi, propenilamino, butenilamino, propilidenamino, butilidenamino, propeniloxicarbonilo, buteniloxicarbonilo, propinilo, butinilo, propiniloxi, butiniloxi, propinilamino, butinilamino, propiniloxicarbonilo o butiniloxicarbonilo substituidos respectivamente, en caso dado, por flúor o por cloro, ciclopropilo, ciclobutilo, ciclopentilo, ciclohexilo, ciclopropiloxi, ciclobutiloxi, ciclopentiloxi, ciclohexiloxi, ciclopropilmetilo, ciclobutilmetilo, ciclopentilmetilo, ciclohexilmetilo, ciclopropilmetoxi, ciclobutilmetoxi, ciclopentilmetoxi, ciclohexilmetoxi, ciclopentilidenamino, ciclohexilidenamino, ciclopentiloxicarbonilo, ciclohexiloxicarbonilo, ciclopentilmetoxicarbonilo o ciclohexilmetoxicarbonilo significa, substituidos respectivamente, en caso dado, por flúor, por cloro, por ciano, por carboxi, por metilo, por etilo, por n- o i-propilo, por metoxicarbonilo o por etoxicarbonilo, o significa fenilo, feniloxi, bencilo, feniletilo, benciloxi, feniloxicarbonilo, benciloxicarbonilo , substituidos respectivamente, en caso dado, por nitro, por ciano, por carboxi, por flúor, por cloro, por bromo, por metilo, por etilo, por n- o i-propilo, por triflúormetilo, por metoxi, por etoxi, por n- o i-propoxi, por diflúormetoxi, por triflúormetoxi, por metoxicarbonilo y/o por etoxicarbonilo, pirrolilo, pirazolilo, imidazolilo, triazolilo, furilo, tienilo, oxazolilo, isoxazolilo, tiazolilo, isotiazolilo, oxadiazolilo, tiadiazolilo, piridinilo, pirimidinilo, triazinilo, pirazolilmetilo, furilmetilo, tienilmetilo, oxazolilmetilo, isoxazolmetilo, tiazolmetilo, piridinilmetilo, pirimidinilmetilo, pirazolmetoxi, furilmetoxi o piridilmetoxi, (hidrogenados en caso dado respectivamente total o parcialmente)means hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, means, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i- s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- o i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- o i-propylamino, n-, i-, s- o t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- o i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl respectively substituted, if necessary, by fluorine, by chlorine, by methoxy or by ethoxy, it means propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenamino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butyloxy, propylamino, butylamino, propynyloxycarbonyl or butynyloxycarbonyl respectively substituted, if necessary, by fluorine or chlorine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylidenamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl means, substituted respectively, if necessary, by fluorine, by chlorine, by cyano, by carboxy, by methyl, for ethyl, for n- or i-propyl, for methoxycarbonyl or ethoxycarbonyl, or means phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, substituted respectively, where appropriate, by nitro, by cyano, by carboxy, by fluorine, by chlorine, by bromine, by methyl, for ethyl, for n- or i-propyl, for trifluoromethyl, by methoxy, by ethoxy, by n- or i-propoxy, by difluoromethoxy, by trifluoromethoxy, by methoxycarbonyl and / or by ethoxycarbonyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolmethoxy, furylmethoxy or pyridylmethoxy, (hydrogenated if appropriate respectively total or partially)
R^{3}R 3
significa hidrógeno, flúor o cloro.means hydrogen, fluorine or chlorine.
3. Compuestos según la reivindicación 1, caracterizados porque3. Compounds according to claim 1, characterized in that
R^{1}R1
significa flúor,means fluorine,
R^{2}R2
significa -NH-SO_{2}-C_{2}H_{5},it means -NH-SO 2 -C 2 H 5,
R^{3}R 3
significa hidrógeno,means hydrogen,
Q^{1}Q1
significa -CO-,means -CO-,
R^{6}R 6
significa triflúormetilo, ymeans trifluoromethyl, and
R^{7}R 7
significa metilo.Methyl means.
4. Procedimiento para la obtención de amidas substituidas de ácidos tiocarboxílicos, aromáticas, según una de las reivindicaciones 1 a 3, caracterizado porque se hacen reaccionar nitrilos aromáticos, substituidos, de la fórmula general (II)4. Process for obtaining substituted amides of aromatic thiocarboxylic acids according to one of claims 1 to 3, characterized in that aromatic, substituted nitriles of the general formula (II) are reacted 232. 3 en la quein the that R^{1}, R^{2}, R^{3} y Z tienen los significados indicados en las reivindicaciones 1 a 3,R 1, R 2, R 3 and Z they have the meanings indicated in claims 1 to 3, con ácido sulfhídrico (sulfuro de hidrógeno, H_{2}S) o con tioacetamida en caso dado en presencia de un agente auxiliar de la reacción y en caso dado en presencia de un diluyente.with hydrogen sulfide ( hydrogen, H 2 S) or with thioacetamide if necessary in the presence of an auxiliary reaction agent and if necessary in the presence of a diluent 5. Procedimiento para la lucha contra las plantas indeseables, caracterizado porque se dejan actuar sobre las plantas indeseables y/o sobre su medio ambiente amidas substituidas de ácidos tiocarboxílicos, aromáticas, de la fórmula general (I) según una de las reivindicaciones 1 a 3.5. Method for combating undesirable plants, characterized in that amides substituted by aromatic thiocarboxylic acids of the general formula (I) according to one of claims 1 to 3 are allowed to act on undesirable plants and / or their environment. . 6. Empleo de amidas substituidas de ácidos tiocarboxílicos, según una de las reivindicaciones 1 a 3, para la lucha contra las plantas indeseables.6. Use of acid substituted amides thiocarboxylic, according to one of claims 1 to 3, for the Fight against undesirable plants. 7. Procedimiento para la obtención de agentes herbicidas, caracterizado porque se mezclan amidas substituidas de ácidos tiocarboxílicos, aromáticas, según una de las reivindicaciones 1 a 3 con extendedores y/o con substancias tensioactivas.7. Method for obtaining herbicidal agents, characterized in that substituted amides of aromatic thiocarboxylic acids are mixed according to one of claims 1 to 3 with extenders and / or with surfactants. 8. Agentes herbicidas caracterizados porque tienen un contenido en al menos una amida substituida de ácido tiocarboxílico, aromática, según una de las reivindicaciones 1 a 4.8. Herbicidal agents characterized in that they contain at least one substituted amide of aromatic thiocarboxylic acid, according to one of claims 1 to 4.
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CN1113875C (en) * 1994-05-04 2003-07-09 拜尔公司 Substituted aromatic thiocarboxylic acid amides and their use as herbicides

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US6077813A (en) 2000-06-20
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